Regioselective and Enantioselective Hydroformylation of Dialkylacrylamides

Advanced Synthesis and Catalysis - Tập 352 Số 6 - Trang 1047-1054 - 2010
Gary M. Noonan1, David J. Newton1, Christopher J. Cobley2, Andrés Suárez3, Antonio Pizzano3, Matthew L. Clarke1
1School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, KY16 9ST, Fife, U.K. Fax: (+44)-(0)1334-463-808
2Chirotech Technology Limited, Dr. Reddy's Laboratories, 162 Cambridge Science Park, Milton Road, Cambridge, CB4 0GH, U.K.
3Instituto de Investigaciones Químicas, Consejo Superior de Investigaciones Científicas and Universidad de Sevilla, Avda Américo Vespucio n° 49, Isla de la Cartuja, 41092 Sevilla, Spain

Tóm tắt

AbstractDimethylacrylamide can be hydroformylated with very high chemo‐ and regioselectivity. Asymmetric hydroformylation of this substrate is possible, provided steps are taken to minimise racemisation of the aldehyde products, and this work demonstrates the effect of various conditions and variables on racemisation. Using the Landis diazaphospholane ligands up to 68% ee can be realised under very mild conditions. Other dialkylacrylamides were also hydroformylated under mild conditions giving similar or better enantioselectivities, including the Weinreb amide of acrylic acid (71% ee), and the asymmetric hydroformylation of diethylacrylamide producing the chiral aldehyde with up to 82% ee.

Từ khóa


Tài liệu tham khảo

 

Leeuwen P. W. N. M. Van, 2000, Rhodium Catalysed Hydroformylation

10.1016/j.ccr.2003.02.001

10.1021/cr00039a008

10.1016/j.tetasy.2004.04.039

10.2174/1385272053764980

10.1055/s-2001-9739

10.1021/ar7001039

 

10.1021/ar000060

10.1021/ja00040a008

10.1021/ja00058a079

10.1002/1521-3757(20010917)113:18<3505::AID-ANGE3505>3.0.CO;2-I

10.1002/1521-3773(20010917)40:18<3408::AID-ANIE3408>3.0.CO;2-A

10.1016/1381-1169(95)00130-1

10.1021/ja0348997

 

10.1002/1521-3765(20010716)7:14<3106::AID-CHEM3106>3.0.CO;2-Y

10.1039/b418259f

10.1039/B315709A

10.1021/om00001a010

Some recent tandem processes:

10.1039/b911612e

10.1002/adsc.200800720

10.1002/adsc.200700160

10.1002/adsc.200700216

Reviews on tandem processes:

10.1021/cr970413r

10.1007/3418_017

10.1002/1521-3765(20010716)7:14<3086::AID-CHEM3086>3.0.CO;2-O

10.1021/jo040128p

10.1021/ol0487938

10.1002/1521-3757(20001117)112:22<4272::AID-ANGE4272>3.0.CO;2-X

10.1002/1521-3773(20001117)39:22<4106::AID-ANIE4106>3.0.CO;2-L

J. E.Babin G. T.Whiteker PatentWO93/03839 1993.

10.1021/ja970049d

10.1021/ja057065s

10.1002/adsc.200390053

10.1021/ja050148o

10.1002/ange.200501478

10.1002/anie.200501478

 

10.1021/om020140c

10.1021/om050885t

10.1021/om700744b

 

10.1002/chem.200600914

10.1016/j.tetlet.2004.03.168

10.1021/ja991175f

 

10.1016/0022-328X(90)85478-H

10.1039/b510813f

10.1021/ol051174u

 

10.1039/b616918j

unpublished results.

10.1039/b502378e

10.1021/ol0706004

Thông tin
Thông tin xuất bản

Advanced Synthesis and Catalysis

Tập 352 Số 6

1047-1054

Thông tin tác giả